CS235971B2 - Fungicide agent and method of effective substances production - Google Patents
Fungicide agent and method of effective substances production Download PDFInfo
- Publication number
- CS235971B2 CS235971B2 CS827905A CS790582A CS235971B2 CS 235971 B2 CS235971 B2 CS 235971B2 CS 827905 A CS827905 A CS 827905A CS 790582 A CS790582 A CS 790582A CS 235971 B2 CS235971 B2 CS 235971B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- alkyl
- acid
- compounds
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000000126 substance Substances 0.000 title description 8
- 239000000417 fungicide Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 229910052751 metal Chemical class 0.000 claims abstract description 19
- 239000002184 metal Chemical class 0.000 claims abstract description 19
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000004480 active ingredient Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 claims description 2
- 229910052783 alkali metal Chemical group 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 239000011737 fluorine Chemical group 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- CLBGIOQSOGUCTA-UHFFFAOYSA-N 2-[(2-phenyl-1,3-dioxolan-2-yl)methyl]-1h-imidazole Chemical class O1CCOC1(C=1C=CC=CC=1)CC1=NC=CN1 CLBGIOQSOGUCTA-UHFFFAOYSA-N 0.000 abstract description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 20
- 239000013543 active substance Substances 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- -1 dusts Substances 0.000 description 11
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
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- 240000005979 Hordeum vulgare Species 0.000 description 7
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 239000006185 dispersion Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical class [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813144318 DE3144318A1 (de) | 1981-11-07 | 1981-11-07 | 2-imidazolylmethyl-2-phenyl-1, 3-dioxolane, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235971B2 true CS235971B2 (en) | 1985-05-15 |
Family
ID=6145891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS827905A CS235971B2 (en) | 1981-11-07 | 1982-11-05 | Fungicide agent and method of effective substances production |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0080071B1 (en, 2012) |
| JP (1) | JPS5888377A (en, 2012) |
| AT (1) | ATE27158T1 (en, 2012) |
| AU (1) | AU555638B2 (en, 2012) |
| BR (1) | BR8206434A (en, 2012) |
| CA (1) | CA1187085A (en, 2012) |
| CS (1) | CS235971B2 (en, 2012) |
| DD (1) | DD208534A5 (en, 2012) |
| DE (2) | DE3144318A1 (en, 2012) |
| DK (1) | DK494482A (en, 2012) |
| ES (1) | ES517158A0 (en, 2012) |
| GR (1) | GR77371B (en, 2012) |
| HU (1) | HU188333B (en, 2012) |
| IL (1) | IL67178A (en, 2012) |
| NZ (1) | NZ202385A (en, 2012) |
| PL (1) | PL133350B1 (en, 2012) |
| PT (1) | PT75759B (en, 2012) |
| ZA (1) | ZA828134B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI77458C (fi) * | 1981-05-12 | 1989-03-10 | Ciba Geigy Ag | Nya mikrobicida arylfenyleterderivat, foerfarande foer deras framstaellning och deras anvaendning. |
| FI834141A7 (fi) * | 1982-11-16 | 1984-05-17 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya arylfenyleterderivat. |
| ZA853066B (en) * | 1984-05-02 | 1985-12-24 | Uniroyal Inc | Substituted imidazoles and triazoles |
| AU575163B2 (en) * | 1984-05-09 | 1988-07-21 | Hunter Douglas Limited | Roof insert |
| IT1186784B (it) * | 1985-11-04 | 1987-12-16 | Montedison Spa | Azoliderivati ad attivita' antufungina |
| DE3914632A1 (de) * | 1989-05-03 | 1990-11-08 | Basf Ag | 1-hydroxi-azolverbindungen und diese enthaltende fungizide |
| US5274108A (en) * | 1992-06-18 | 1993-12-28 | Syntex (U.S.A.) Inc. | Process for preparing 1,3-dioxolane derivatives |
| TW457240B (en) * | 1995-04-20 | 2001-10-01 | Janssen Pharmaceutica Nv | Novel triazolones as apolipoprotein-B synthesis inhibitors |
| RU2146447C1 (ru) * | 1999-02-10 | 2000-03-20 | Кубанский государственный технологический университет | Средство для одновременной активации прорастания семян пшеницы и повышения устойчивости проростков к водному стрессу |
| US7053248B2 (en) | 2002-08-09 | 2006-05-30 | Central Glass Company, Limited | Process for producing trifluoromethyl- substituted 2- alkoxyacetophenone derivatives |
| EP2745691A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted imidazole compounds and their use as fungicides |
| EP3519404A1 (en) * | 2016-09-29 | 2019-08-07 | Bayer CropScience Aktiengesellschaft | 5-substituted imidazolylmethyldioxolane derivatives as fungiciides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3575999A (en) * | 1968-08-19 | 1971-04-20 | Janssen Pharmaceutica Nv | Ketal derivatives of imidazole |
| CA1065873A (en) * | 1975-01-27 | 1979-11-06 | Janssen Pharmaceutica Naamloze Vennootschap | Imidazole derivatives |
| EP0006722B1 (en) * | 1978-07-03 | 1984-09-05 | Janssen Pharmaceutica N.V. | Derivatives of (4-(piperazin-1-yl-phenyloxymethyl)-1.3-dioxolan-2-ylmethyl)-1h-imidazoles and -1h-1.2.4-triazoles, their preparation and use as fungicides and bactericides |
| AU526321B2 (en) * | 1978-07-24 | 1983-01-06 | Janssen Pharmaceutica N.V. | 1-(2-aryl-4,5-disubstituted-1,3-dioxolan-2-yl-methyl)-1h- imidazoles and 1h-1,2,4-triazoles |
| CH637392A5 (en) * | 1978-07-24 | 1983-07-29 | Janssen Pharmaceutica Nv | 2-Phenyl-2-azolylmethyl-cyclohexa(d)-1,3-dioxolane derivatives, processes for their preparation, compositions containing these active substances as microbicides, and their use |
| CA1173449A (en) * | 1979-11-16 | 1984-08-28 | Adolf Hubele | 1-¬2-(4-diphenyl)ethyl|-1h-azolylketals |
| ZA823225B (en) * | 1981-05-12 | 1983-03-30 | Ciba Geigy | Novel microbicidal arylphenyl ether derivatives,production thereof and the use thereof |
| FI77458C (fi) * | 1981-05-12 | 1989-03-10 | Ciba Geigy Ag | Nya mikrobicida arylfenyleterderivat, foerfarande foer deras framstaellning och deras anvaendning. |
-
1981
- 1981-11-07 DE DE19813144318 patent/DE3144318A1/de not_active Withdrawn
-
1982
- 1982-10-28 AT AT82109961T patent/ATE27158T1/de not_active IP Right Cessation
- 1982-10-28 EP EP82109961A patent/EP0080071B1/de not_active Expired
- 1982-10-28 PT PT75759A patent/PT75759B/pt unknown
- 1982-10-28 DE DE8282109961T patent/DE3276315D1/de not_active Expired
- 1982-10-29 AU AU90018/82A patent/AU555638B2/en not_active Ceased
- 1982-11-02 JP JP57191946A patent/JPS5888377A/ja active Granted
- 1982-11-04 DD DD82244560A patent/DD208534A5/de unknown
- 1982-11-04 IL IL67178A patent/IL67178A/xx unknown
- 1982-11-04 NZ NZ202385A patent/NZ202385A/en unknown
- 1982-11-04 HU HU823553A patent/HU188333B/hu not_active IP Right Cessation
- 1982-11-05 CA CA000414986A patent/CA1187085A/en not_active Expired
- 1982-11-05 ES ES517158A patent/ES517158A0/es active Granted
- 1982-11-05 DK DK494482A patent/DK494482A/da not_active Application Discontinuation
- 1982-11-05 CS CS827905A patent/CS235971B2/cs unknown
- 1982-11-05 ZA ZA828134A patent/ZA828134B/xx unknown
- 1982-11-05 GR GR69731A patent/GR77371B/el unknown
- 1982-11-05 PL PL1982238886A patent/PL133350B1/pl unknown
- 1982-11-05 BR BR8206434A patent/BR8206434A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK494482A (da) | 1983-05-08 |
| ES8307799A1 (es) | 1983-08-01 |
| EP0080071A3 (en) | 1983-09-07 |
| ZA828134B (en) | 1983-09-28 |
| IL67178A (en) | 1986-12-31 |
| JPS5888377A (ja) | 1983-05-26 |
| GR77371B (en, 2012) | 1984-09-11 |
| PT75759A (en) | 1982-11-01 |
| DE3144318A1 (de) | 1983-05-19 |
| DD208534A5 (de) | 1984-04-04 |
| PT75759B (en) | 1985-07-26 |
| PL133350B1 (en) | 1985-05-31 |
| BR8206434A (pt) | 1983-09-27 |
| DE3276315D1 (en) | 1987-06-19 |
| ES517158A0 (es) | 1983-08-01 |
| AU9001882A (en) | 1983-05-12 |
| IL67178A0 (en) | 1983-03-31 |
| EP0080071A2 (de) | 1983-06-01 |
| NZ202385A (en) | 1985-02-28 |
| HU188333B (en) | 1986-04-28 |
| AU555638B2 (en) | 1986-10-02 |
| JPH0422913B2 (en, 2012) | 1992-04-20 |
| CA1187085A (en) | 1985-05-14 |
| EP0080071B1 (de) | 1987-05-13 |
| PL238886A1 (en) | 1983-06-06 |
| ATE27158T1 (de) | 1987-05-15 |
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